DE19744135C1 - Medical implants coated with epothilone - Google Patents
Medical implants coated with epothiloneInfo
- Publication number
- DE19744135C1 DE19744135C1 DE19744135A DE19744135A DE19744135C1 DE 19744135 C1 DE19744135 C1 DE 19744135C1 DE 19744135 A DE19744135 A DE 19744135A DE 19744135 A DE19744135 A DE 19744135A DE 19744135 C1 DE19744135 C1 DE 19744135C1
- Authority
- DE
- Germany
- Prior art keywords
- epothilone
- polymer
- medical implants
- stent
- active ingredient
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
- Expired - Lifetime
Links
Classifications
-
- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09D—COATING COMPOSITIONS, e.g. PAINTS, VARNISHES OR LACQUERS; FILLING PASTES; CHEMICAL PAINT OR INK REMOVERS; INKS; CORRECTING FLUIDS; WOODSTAINS; PASTES OR SOLIDS FOR COLOURING OR PRINTING; USE OF MATERIALS THEREFOR
- C09D175/00—Coating compositions based on polyureas or polyurethanes; Coating compositions based on derivatives of such polymers
- C09D175/04—Polyurethanes
- C09D175/08—Polyurethanes from polyethers
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61L—METHODS OR APPARATUS FOR STERILISING MATERIALS OR OBJECTS IN GENERAL; DISINFECTION, STERILISATION OR DEODORISATION OF AIR; CHEMICAL ASPECTS OF BANDAGES, DRESSINGS, ABSORBENT PADS OR SURGICAL ARTICLES; MATERIALS FOR BANDAGES, DRESSINGS, ABSORBENT PADS OR SURGICAL ARTICLES
- A61L31/00—Materials for other surgical articles, e.g. stents, stent-grafts, shunts, surgical drapes, guide wires, materials for adhesion prevention, occluding devices, surgical gloves, tissue fixation devices
- A61L31/08—Materials for coatings
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61L—METHODS OR APPARATUS FOR STERILISING MATERIALS OR OBJECTS IN GENERAL; DISINFECTION, STERILISATION OR DEODORISATION OF AIR; CHEMICAL ASPECTS OF BANDAGES, DRESSINGS, ABSORBENT PADS OR SURGICAL ARTICLES; MATERIALS FOR BANDAGES, DRESSINGS, ABSORBENT PADS OR SURGICAL ARTICLES
- A61L31/00—Materials for other surgical articles, e.g. stents, stent-grafts, shunts, surgical drapes, guide wires, materials for adhesion prevention, occluding devices, surgical gloves, tissue fixation devices
- A61L31/08—Materials for coatings
- A61L31/10—Macromolecular materials
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61L—METHODS OR APPARATUS FOR STERILISING MATERIALS OR OBJECTS IN GENERAL; DISINFECTION, STERILISATION OR DEODORISATION OF AIR; CHEMICAL ASPECTS OF BANDAGES, DRESSINGS, ABSORBENT PADS OR SURGICAL ARTICLES; MATERIALS FOR BANDAGES, DRESSINGS, ABSORBENT PADS OR SURGICAL ARTICLES
- A61L31/00—Materials for other surgical articles, e.g. stents, stent-grafts, shunts, surgical drapes, guide wires, materials for adhesion prevention, occluding devices, surgical gloves, tissue fixation devices
- A61L31/14—Materials characterised by their function or physical properties, e.g. injectable or lubricating compositions, shape-memory materials, surface modified materials
- A61L31/16—Biologically active materials, e.g. therapeutic substances
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61L—METHODS OR APPARATUS FOR STERILISING MATERIALS OR OBJECTS IN GENERAL; DISINFECTION, STERILISATION OR DEODORISATION OF AIR; CHEMICAL ASPECTS OF BANDAGES, DRESSINGS, ABSORBENT PADS OR SURGICAL ARTICLES; MATERIALS FOR BANDAGES, DRESSINGS, ABSORBENT PADS OR SURGICAL ARTICLES
- A61L2300/00—Biologically active materials used in bandages, wound dressings, absorbent pads or medical devices
- A61L2300/40—Biologically active materials used in bandages, wound dressings, absorbent pads or medical devices characterised by a specific therapeutic activity or mode of action
- A61L2300/416—Anti-neoplastic or anti-proliferative or anti-restenosis or anti-angiogenic agents, e.g. paclitaxel, sirolimus
Abstract
Description
Die Erfindung betrifft Mittel zur Herstellung von beschichteten, wirkstoffabgebenden medizinischen Implantaten, z. B. Stents, die so präparierten Implantate, Verfahren zu ihrer Herstellung und ihre Verwendung zur Restenoseprophylaxe.The invention relates to agents for the production of coated, drug-delivering medical implants, e.g. B. stents that so prepared implants, processes for their manufacture and their Use for restenosis prophylaxis.
Implantate, vor allem Stents sind Stand der Technik (Pschyrembel, Klinisches Wörterbuch 257. Auflage, Verlag W. de Gruyter). Stents sind selbstexpandierende Endoprothesen, die die Offenhaltung gangartiger Strukturen in Körpern von Menschen oder Tieren ermöglichen (z. B. Gefäß-, Ösophagus-, Trachea-, Gallengangstent). Sie werden als palliative Maßnahme bei Verengungen durch Verschluß (z. B. Atherosklerose) oder Druck von außen (z. B. bei Tumoren) verwendet. Radioaktive Stents werden beispielsweise nach gefäßchirurgischen oder interventionell radiologischen Eingriffen (z. B. Ballonangioplastie) zur Restenoseprophylaxe eingesetzt. Implants, especially stents, are state of the art (pschyrembel, Clinical Dictionary 257th edition, published by W. de Gruyter). Are stents self-expanding endoprostheses that keep the gait open Enable structures in human or animal bodies (e.g. vascular, Esophageal, tracheal, biliary stent). They are called palliative Measure for narrowing due to occlusion (e.g. atherosclerosis) or External pressure (e.g. for tumors) is used. Radioactive stents will be for example after vascular surgery or interventional radiological Interventions (e.g. balloon angioplasty) used for prophylaxis of restenosis.
So ist z. B. aus der Internationalen Patentanmeldung WO 94/13268 ein Stent bekannt, der im Körper nach und nach einen Wirkstoff frei setzt. Aus dem Patent US 5,599,552 ist eine Polymerzusammensetzung bekannt, die im Körper gelieren kann. In fester Form stellt sie ein Implantat dar, das nach und nach einen Wirkstoff freisetzen kann.So z. B. from the international patent application WO 94/13268 a stent known that gradually releases an active ingredient in the body. From the Patent US 5,599,552 a polymer composition is known which in Body can gel. In solid form, it represents an implant that follows and after can release an active ingredient.
Es besteht nun das Problem, daß das medizinische Implantat für den Organismus einen Fremdkörper darstellt und es zu Unverträglichkeits reaktionen kommt.There is now the problem that the medical implant for the Organism represents a foreign body and it causes intolerance reactions come.
Aufgabe der vorliegenden Erfindung ist es daher, medizinische Implantate zur Verfügung zu stellen, die besser verträglich sind als herkömmliche medizinische Implantate.The object of the present invention is therefore to provide medical implants to provide more tolerable than conventional medical implants.
Diese Aufgabe wird durch die nachfolgend beschriebenen medizinischen Implantate gelöst, wie sie in den Patentansprüchen gekennzeichnet sind.This task is accomplished through the medical described below Implants solved as they are characterized in the claims.
Die oben geschilderte Aufgabe wird erfindungsgemäß dadurch gelöst, daß die Oberfläche der medizinischen Implantate mit einem Polymer beschichtet wird, in das mindestens ein Wirkstoff auf der Basis von Epothilon, z. B. Epothilon A oder B oder ein Derivat von Epothilon, sowie eventuell weitere Wirkstoffe, wie z. B. thromboseverhindernde Substanzen und/oder Östrogene und/oder Kortikosteroide eingearbeitet sind. Epothilon und seine Synthese sind aus der Literatur bekannt (Höfle et al., Angew. Chem. 108: 1671-3 (1996), Schinzer et al., Angew. Chem. 109 : 543-4 (1997)). In einer besonderen Ausführungsform der Erfindung kann der Wirkstoff Epothilon auch ohne Polymer direkt auf das medizinische Implantat aufgebracht werden.The above-described object is achieved in that the surface of the medical implants is coated with a polymer is, in which at least one active ingredient based on epothilone, for. B. Epothilon A or B or a derivative of Epothilon, and possibly others Active ingredients, such as B. thrombosis-preventing substances and / or Estrogens and / or corticosteroids are incorporated. Epothilon and his Synthesis are known from the literature (Höfle et al., Angew. Chem. 108: 1671-3 (1996), Schinzer et al., Angew. Chem. 109: 543-4 (1997)). In a In a special embodiment of the invention, the active ingredient epothilone also applied directly to the medical implant without polymer become.
Die erfindungsgemäße Vorrichtung besteht somit aus dem medizinischen Implantat, evtl. aus einem Polymer auf der Oberfläche des Implantats und mindestens einem Wirkstoff aus der Klasse der Epothilone. The device according to the invention thus consists of the medical Implant, possibly made of a polymer on the surface of the implant and at least one active ingredient from the class of the epothilones.
Die Erfindung betrifft aber auch Vorrichtungen, Substanzen, Lösungen und Behältnisse für die erfindungsgemäße Beschichtung von Implantaten, z. B. in Form eines Kits. Derartige Kits können vom Mediziner vor Ort für die Beschichtung von ausgewählten Implantaten verwendet werden.The invention also relates to devices, substances, solutions and Containers for the coating of implants according to the invention, for. B. in Form of a kit. Such kits can be obtained from the local doctor for the Coating of selected implants can be used.
Als Grundkörper können die handelsüblichen Implantante verwendet werden, bei den Stents z. B. ein Wiktor-Stent, ein Strecker-Stent oder ein Palmaz- Schatz Stent.The commercially available implants can be used as the base body, in the stents z. B. a Wiktor stent, a Strecker stent or a Palmaz Treasure stent.
Als Polymere kommen beispielsweise Polyurethane, Polylactide, gemischte Polylactid-glycolide oder andere, in der Literatur beschriebene Polymere in Betracht.Examples of polymers are polyurethanes, polylactides, mixed Polylactide glycolide or other polymers described in the literature in Consideration.
Die erfindungsgemäßen Implantate - beschrieben an Hand von Stents - können beispielhaft folgendermaßen hergestellt werden:The implants according to the invention - described with the aid of stents - can be produced as follows:
1.1 Ein unbeschichteter Stent wird zunächst mit einem Polymer (z. B. ein
Polyurethan, erhältlich aus der Reaktion eines amphiphilen Polyethers,
Diphenylmethan-4-4'-diisocyanat und Butandiol) beschichtet. Dazu
wird das Polymer in einem Lösemittel (z. B. Chloroform) gelöst und der
Stent in die Polymerlösung eingetaucht. Nach Entnahme des Stents
aus der Polymerlösung wird er in einer Trockenkammer bei
Raumtemperatur getrocknet. Anschließend wird der Stent in eine
Lösung von Epothilon A in Ethylacetat getaucht und getrocknet.
Dieser Prozeß kann - je nach der gewünschten Beladung mit Epothilon -
mehrfach wiederholt werden. Der wirkstoffbeladene Stent ist
gebrauchsfertig.1.1 An uncoated stent is first coated with a polymer (e.g. a polyurethane, obtainable from the reaction of an amphiphilic polyether, diphenylmethane 4-4'-diisocyanate and butanediol). For this purpose, the polymer is dissolved in a solvent (e.g. chloroform) and the stent is immersed in the polymer solution. After the stent has been removed from the polymer solution, it is dried in a drying chamber at room temperature. The stent is then immersed in a solution of Epothilon A in ethyl acetate and dried.
This process can be repeated several times, depending on the desired loading with epothilone. The active ingredient-loaded stent is ready for use.
1.2 In einer Variante des Verfahrens nach 1.1 wird folgendermaßen vorgegangen: Die Beschichtung mit Polymer und Wirkstoff erfolgt abwechselnd, so daß abwechselnd Schichten mit Polymer und Epothilon entstehen.1.2 In a variant of the method according to 1.1 is as follows proceeded: The coating with polymer and active ingredient takes place alternately, so that alternately layers with polymer and Epothilon arise.
1.3. Eine weitere Möglichkeit besteht darin, das Polymer und den Wirkstoff, Epothilon, im selben Lösungsmittel, z. B. Chloroform oder Ethylacetat zu lösen und so in einem Schritt auf den Stent aufzubringen. 1.3. Another possibility is the polymer and the Active ingredient, epothilone, in the same solvent, e.g. B. chloroform or Dissolve ethyl acetate and so on the stent in one step to apply.
1.4. In einer weiteren Variante kann zusätzlich zu Epothilon oder einem Epothilon-Derivat ein anderer Wirkstoff aufgebracht werden. Beispiele für andere Wirkstoffe sind thromboseverhindernde Arzneimittel, wie z. B. Iloprost, Östrogene, wie zum Beispiel Ethinylöstradiol oder Kortikoide, wie z. B. Dexamethason, Fluocortolon, Difluorcortolon oder deren Ester.1.4. In a further variant, in addition to epothilone or a Another active ingredient can be applied to epothilone derivative. Examples for other active substances are thrombosis-preventing drugs, such as e.g. B. Iloprost, estrogens, such as ethinyl estradiol or Corticoids such as B. Dexamethasone, Fluocortolon, Difluorcortolon or their esters.
2.1 Ein unbeschichteter Stent kann zunächst mit einem Polymer (z. B. ein Polyurethan, erhältlich aus der Reaktion eines amphiphilen Polyethers, Diphenylmethan-4-4'-diisocyanat und Butandiol) beschichtet werden. Dieses Polymer ist derartig modifiziert, daß es an der Oberfläche Cyclodextrin trägt. Das Polymer wird in einem Lösemittel (z. B. Chloroform) gelöst und der Stent in die Polymerlösung eingetaucht. Nach Entnahme des Stents aus der Polymerlösung wird er in einer Trockenkammer bei Raumtemperatur getrocknet. Die "Aktivierung" des Stents erfolgt nun dadurch, daß der derartig modifizierte Stent in eine wäßrige Lösung von Epothilon getaucht wird. Dabei wird der Wirkstoff in das Cyclodextrin eingebaut. Der Stent ist nun gebrauchsfertig.2.1 An uncoated stent can first be coated with a polymer (e.g. a Polyurethane, obtainable from the reaction of an amphiphilic polyether, Diphenylmethane-4-4'-diisocyanate and butanediol) can be coated. This polymer is modified so that it is on the surface Cyclodextrin carries. The polymer is in a solvent (e.g. Chloroform) and the stent is immersed in the polymer solution. After removing the stent from the polymer solution, it is placed in a Drying chamber dried at room temperature. The "activation" of the stent is now done in that the modified stent in an aqueous solution of epothilone is immersed. The Active ingredient built into the cyclodextrin. The stent is now ready to use.
Die oben beschriebenen Verfahren werden im allgemeinen bei Temperaturen von 0-80°C durchgeführt. Bei der Beschichtung des Stents mit dem Polymer können in Abhängigkeit von dem jeweiligen Polymer Lösemittel eingesetzt werden. Bei Einsatz eines nichtwäßrigen Lösemittels soll dieses vor der Implantation entfernt werden.The processes described above are generally carried out at temperatures from 0-80 ° C. When coating the stent with the polymer can be used depending on the particular polymer solvent become. When using a non-aqueous solvent, this should be done before Implantation to be removed.
Die nötigen Arbeitsgänge zur Durchführung der oben prinzipiell beschriebenen Verfahren sind dem Fachmann bekannt. Spezielle Ausführungsformen sind detailliert in den Beispielen beschrieben.The necessary operations to carry out the above in principle The methods described are known to the person skilled in the art. Specific Embodiments are described in detail in the examples.
Die erfindungsgemäßen Implantate lösen die eingangs beschriebene Aufgabe. Die erfindungsgemäßen Implantate sind physiologisch gut verträglich. The implants according to the invention solve the one described at the beginning Task. The implants according to the invention are physiologically good compatible.
Der besondere Vorteil der erfindungsgemäßen Implantate ist, daß der Mediziner vor Ort einen Stent nach seinen Bedürfnissen auswählen und den ausgewählen Stent dann durch das beschriebene Verfahren aktivieren kann. Die wenigen dazu nötigen Stoffe und Lösungen können entsprechend vorbereitet angeliefert werden, so daß der entsprechende Mediziner nur noch den unbeschichteten Stent in der vorgegebenen Reihenfolge in die einzelnen Lösungen tauchen muß. Die Erfindung betrifft somit auch solche für die erfindungsgemäßen Verfahren vorbereiteten Stoffe, Lösungen und Zubereitungen (Kits) und Behältnisse.The particular advantage of the implants according to the invention is that the Local physicians select a stent according to their needs and the selected stent can then be activated by the described method. The few substances and solutions required for this can be used accordingly be delivered prepared, so that the corresponding medical professional only the uncoated stent in the order shown individual solutions must dive. The invention thus also relates to such substances, solutions and prepared for the method according to the invention Preparations (kits) and containers.
Die folgenden Beispiele sollen den Erfindungsgegenstand erläutern, ohne ihn auf diese beschränken zu wollen.The following examples are intended to illustrate the subject matter of the invention without it want to limit to this.
Als Polymer wird Polyurethan verwendet, das durch Reaktion eines amphiphilen Polyethers, Diphenylmethan-4,4'-diisocyanat und Butandiol als Kettenverlängerer erhältlich ist. Die Stents werden dadurch beschichtet, daß sie in eine 5%ige Chloroform-Lösung des Polymers eingetaucht werden. Danach läßt man sie einer Reinraum-Trockenkammer bei Zimmertemperatur trocknen. Die durchschnittliche Schichtdicke beträgt 20 µm. Die Belegung mit Epothilon A erfolgt durch Eintauchen des polymerbeschichteten Stents in eine wäßrige Lösung von Epothilon A (0,5 mg/ml). Nach dem Trocknen ist der Stent gebrauchsfertig.Polyurethane is used as the polymer amphiphilic polyether, diphenylmethane-4,4'-diisocyanate and butanediol as Chain extender is available. The stents are coated in that they are immersed in a 5% chloroform solution of the polymer. Then they are left in a clean room drying chamber at room temperature dry. The average layer thickness is 20 µm. The occupancy with Epothilon A is done by immersing the polymer-coated stent in an aqueous solution of Epothilon A (0.5 mg / ml). After drying the stent is ready for use.
Die Beschichtung des Stents mit dem Polymer und die anschließende Beschichtung mit Epothilon A erfolgt wie unter Beispiel 1 beschrieben. Allerdings wird der Stent jetzt abwechselnd in eine Lösung mit dem Polymer und - nach dem Trocknen - in eine wäßrige Lösung von Epothilon A eingetaucht. Dadurch entsteht ein mehrlagiger Aufbau. Die Menge an inkorporiertem Wirkstoff kann über die Anzahl der Epothilon-haltigen Schichten gesteuert werden. Nach dem letzten Trocknungsgang wird der Stent implantiert. The coating of the stent with the polymer and the subsequent Coating with epothilone A is carried out as described in Example 1. However, the stent is now alternately in solution with the polymer and - after drying - in an aqueous solution of Epothilon A immersed. This creates a multi-layer structure. The amount of Incorporated active ingredient can over the number of epothilone-containing Layers can be controlled. After the last drying cycle, the Implanted stent.
Die Beschichtung erfolgt wie unter Beispiel 2 beschrieben. Allerdings wird der Stent jetzt abwechselnd in eine Lösung mit dem Polymer und - jeweils nach dem Trocknen - in eine wäßrige Lösung von Epothilon A oder Iloprost oder einer Lösung eines Östrogenderivates oder Kortikoids in Chloroform eingetaucht. Die Reihenfolge der Beschichtungsmaterialien (Polymer bzw. Wirkstoff) kann variiert werden. Dadurch entsteht ein mehrlagiger Aufbau. Die Menge an inkorporiertem Wirkstoff kann über die Anzahl der jeweiligen Schichten gesteuert werden. Nach dem letzten Trocknungsgang wird der Stent implantiert.The coating is carried out as described in Example 2. However the stent now alternately in a solution with the polymer and - each after drying - in an aqueous solution of Epothilon A or Iloprost or a solution of an estrogen derivative or corticoid in chloroform immersed. The order of the coating materials (polymer or Active ingredient) can be varied. This creates a multi-layer structure. The amount of active ingredient incorporated can depend on the number of each Layers can be controlled. After the last drying cycle, the Implanted stent.
Claims (14)
Priority Applications (5)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
DE19744135A DE19744135C1 (en) | 1997-09-29 | 1997-09-29 | Medical implants coated with epothilone |
PCT/EP1998/006019 WO1999016416A2 (en) | 1997-09-29 | 1998-09-24 | Coated medical implants, method for producing them, and use of the same for preventing restenosis |
EP98952617A EP1024842A2 (en) | 1997-09-29 | 1998-09-24 | Coated medical implants, method for producing them, and use of the same for preventing restenosis |
JP2000513554A JP2001517543A (en) | 1997-09-29 | 1998-09-24 | Coated medical implant, method for manufacturing the same and use thereof for preventing restenosis |
AU10251/99A AU1025199A (en) | 1997-09-29 | 1998-09-24 | Coated medical implants, method for producing them, and use of the same for preventing restenosis |
Applications Claiming Priority (1)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
DE19744135A DE19744135C1 (en) | 1997-09-29 | 1997-09-29 | Medical implants coated with epothilone |
Publications (1)
Publication Number | Publication Date |
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DE19744135C1 true DE19744135C1 (en) | 1999-03-25 |
Family
ID=7844759
Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
DE19744135A Expired - Lifetime DE19744135C1 (en) | 1997-09-29 | 1997-09-29 | Medical implants coated with epothilone |
Country Status (5)
Country | Link |
---|---|
EP (1) | EP1024842A2 (en) |
JP (1) | JP2001517543A (en) |
AU (1) | AU1025199A (en) |
DE (1) | DE19744135C1 (en) |
WO (1) | WO1999016416A2 (en) |
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EP1179353A1 (en) * | 2000-08-11 | 2002-02-13 | B. Braun Melsungen Ag | Antithrombogenic implants with coating of polyphosphazenes and a pharmacologically active agent |
WO2002064185A2 (en) * | 2001-02-13 | 2002-08-22 | Norbert Sass | Method for reducing secondary complications during the implantation of stents |
EP1270026A1 (en) * | 2001-06-22 | 2003-01-02 | Erik Andersen | Stents comprising vitamin D analogues for restenosis inhibition |
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WO2002065947A3 (en) * | 2001-02-16 | 2003-09-18 | Abbott Lab Vascular Entpr Ltd | Implants with fk506 for prophylaxis and treatment of restonoses |
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ES2378905T3 (en) | 2006-10-10 | 2012-04-19 | Celonova Biosciences, Inc. | Bioprotics heart valve with polyphosphazene |
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US5994341A (en) * | 1993-07-19 | 1999-11-30 | Angiogenesis Technologies, Inc. | Anti-angiogenic Compositions and methods for the treatment of arthritis |
CZ297979B6 (en) * | 1996-03-12 | 2007-05-16 | Pg-Txl Company, L. P. | Composition comprising anti-tumor medicament conjugated to water-soluble polymer, its use in the preparation of a medicament and implantable medical device |
WO1997045105A1 (en) * | 1996-05-24 | 1997-12-04 | Angiotech Pharmaceuticals, Inc. | Compositions and methods for treating or preventing diseases of body passageways |
-
1997
- 1997-09-29 DE DE19744135A patent/DE19744135C1/en not_active Expired - Lifetime
-
1998
- 1998-09-24 EP EP98952617A patent/EP1024842A2/en not_active Withdrawn
- 1998-09-24 JP JP2000513554A patent/JP2001517543A/en active Pending
- 1998-09-24 WO PCT/EP1998/006019 patent/WO1999016416A2/en not_active Application Discontinuation
- 1998-09-24 AU AU10251/99A patent/AU1025199A/en not_active Abandoned
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US7759374B2 (en) | 2002-08-23 | 2010-07-20 | Sloan-Kettering Institute For Cancer Research | Synthesis of epothilones, intermediates thereto and analogues thereof |
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US7875638B2 (en) | 2002-08-23 | 2011-01-25 | Sloan-Kettering Institute For Cancer Research | Synthesis of epothilones, intermediates thereto, analogues and uses thereof |
US8110590B2 (en) | 2002-08-23 | 2012-02-07 | Sloan-Kettering Institute For Cancer Research | Synthesis of epothilones, intermediates thereto and analogues thereof |
US8513429B2 (en) | 2002-08-23 | 2013-08-20 | Sloan-Kettering Insitute For Cancer Research | Synthesis of epothilones, intermediates thereto and analogues thereof |
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Also Published As
Publication number | Publication date |
---|---|
EP1024842A2 (en) | 2000-08-09 |
WO1999016416A3 (en) | 1999-08-05 |
JP2001517543A (en) | 2001-10-09 |
WO1999016416A2 (en) | 1999-04-08 |
AU1025199A (en) | 1999-04-23 |
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